The synthesis of 6‐substituted 1‐deazapurine 2′‐deoxyribonucleosides is described. Glycosylation of the 1‐deazapurine (imidazo[4,5‐b]pyridine) anions with the α‐D‐halogenose 5 gives stereoselectively N7‐ and N9‐ regioisomers. 1H‐NMR NOE and 13C‐NMR spectroscopy are used for unambiguous assignment of isomers, and 15N‐NMR chemical shifts are correlated with σpara Hammett constants and point charges.
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Wenzel et al. (1996) studied this question.
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